I don't expect Halifax to be included in the league from the onset (ie. 2018), but I do see them in the league as an expansion team the following year... or part of the league launch if that is pushed back to 2019.
But, I say this without any insight into negotiations, just a personal thought blurted out.

http://www.mlssoccer.com/post/2015/12/08/armchair-analyst-eight-most-intriguing-names-first-ever-crop-mls-free-agency
In the article above, under #7 Ned Grabavoy, a brief blip on Osorio is made:
"He (Grabavoy) still created 32 chances from open play and completed more than 86 percent of his passes. Of players with 30 or more open play chances created, only Darlington Nagbe and Jonathan Osorio were more accurate in their distribution."
In a defensive system that Floro loves to operate in with our team, I don't see how someone of Jonathan Osorio's creative talents cannot be utilized going the other way, especially for a team that has difficulty creating chances and scoring goals. I'm not vouching that Osorio be a starter, but he should at the very least be included in the roster for important games.
Having done well in our last two matches against Honduras & El Salvador, going forward I truly would like to see Floro urging some more creativity on the counter (if that's the system he wants to stick to) and by not including Oso in that fold would go against the notion of having your strongest team for every game.
When Floro HAS access to Canada's potentially strongest squad, but decides NOT to bring Canada's strongest squad (even if its for personal reasons) then he's NOT coaching for the better of Canada and it's supporters but rather for himself, and I don't think we can fully back Floro because of that.

From cradle to grave clubs... Need more of these. Well-to-do amateur clubs should be able to build 5,000 - 10,000 seat stadiums. Start smaller if you must, and build up/expand later if possible, but start. Can't do it alone? Join forces with other amateur clubs/academies to create a pro team, using your amateur teams as feeders (ie. Sigma with Oakville Blue Devils, or Woodbridge Strikers with Vaughan and/or ANB). I strictly used L1O teams in my example, but any amateur team could be used. A team in Mississauga may or may not be able to hold a pro team on their own. You know what might work better, a regional team ie. Peel. If that's the case don't name the team after Toronto. Represent the area. There's Brampton, Oakville, Mississauga, Burlington (BOMB's), also Milton, Georgetown, Caledon, etc. Could create a Halton-Peel club (likely playing out of Mississauga mind you). I think association with Toronto is part of the issue for a place like Mississauga. People/supporters of franchises see themselves as an extension of the bigger city. If a team was representing and named after the regional community I think it would garner more support.

Something like this would be great, and I think it could work. Not even sure if Sigma (or amalgamated academies) would want to go pro. Sigma+Oakville+ANB+etc joining forces... I've daydreamed about somehow finding enough funds to have a team go pro in the north/east end of the GTA.

BY FAR the best kit we've ever had. I love the Umbro kits, mostly for the quality. I've never put on better tailored kits. Oh Canada sound wave is unique and extra cool. I've always liked a tad bit of black though, even if it was just a trim. But other than that love their stuff!